


This Time, I'll Keep You

by Kleineganz



Series: Next Time... [3]
Category: Supernatural
Genre: Alternate Universe - Canon Divergence, Anal Fingering, Anal Plug, Anal Sex, Blow Jobs, Coming Untouched, Domestic Discipline, Hair-pulling, Kept Dean Winchester, M/M, Pining, Power Imbalance, Spanking, Team Dean Winchester's Red Ass
Language: English
Status: Completed
Published: 2021-02-08
Updated: 2021-02-08
Packaged: 2021-03-13 19:28:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,931
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29283804
Author URL: https://archiveofourown.org/users/Kleineganz/pseuds/Kleineganz
Summary: Dean takes his time considering the idea of becoming Sheriff Novak's kept boy. In the end, he realizes he has nothing left to lose, and only a world of tantalizing pleasure to gain.
Relationships: Castiel/Dean Winchester
Series: Next Time... [3]
Series URL: https://archiveofourown.org/series/2040978
Comments: 11
Kudos: 114





	This Time, I'll Keep You

For the hundredth time, Dean dragged the now crumpled sheets of paper out of his back pocket as he lay back on yet another motel room bed. Unfolding them, he stared at the title as he unbuttoned his jeans and took out his already semi-hard cock.

_Rules, Rights, and Expectations of Becoming a kept boy_

The title alone was enough to get him rock hard in mere moments, as he lazily stroked himself.

#  _Rules_

  1. _A kept boy will submit to his Keeper in all ways._
  2. _A kept boy will never wear clothing inside the home. He must always be naked and available for his Keeper to use._
  3. _A kept boy will wear his Keeper’s collar at all times._
  4. _A kept boy will keep his hole clean, stretched, and lubricated for use by his Keeper. A plug will be worn when the Keeper is not using his boy._
  5. _A kept boy will submit to daily discipline, punishment when disobedient, and provide stress relief as his Keeper requires._



#  _Rights_

  1. _A kept boy has the right to be well fed._
  2. _A kept boy has the right to have a comfortable place to sleep._
  3. _A kept boy has the right to wear clothing outside of the home._
  4. _A kept boy has the right to have friends, as long as they do not interfere with the Keeper’s needs._
  5. _A kept boy has the right to engage his own interests when his Keeper does not have use for him._



#  _Expectations_

  1. _A kept boy is expected to maintain proper hygiene._
  2. _A kept boy is expected to maintain his fitness._
  3. _A kept boy is expected to help with household chores._
  4. _A kept boy is expected to be honest and respectful to his Keeper._
  5. _A kept boy is expected to always put his Keeper’s pleasure before his own._



As he finished reading the pages again, Dean was so aroused it only took a few more hard strokes of his hand before he was coming all over himself. _Damn it, why is the thought of all this so damned hot?_

Dean had been a drifter for so many years now, the Impala his only possession. He’d lived out of the car more often than not over the past several years whenever he couldn’t hustle enough money playing pool to afford a room for the night. Now this kinky-ass sheriff in the middle of bumfuck nowhere was offering him a chance at having a home and some semblance of stability. All in exchange for letting him have his wicked ways with him. He’d never been with a man before the night the sheriff drove him out into the middle of nowhere to rape him. Dean shouldn’t want anything to do with the creep, but after that last time he had to admit to himself, he was addicted to being fucked by the man.

After letting the sheriff fuck him that second time, he tried desperately to get Castiel out of his system. He fucked a bevy of women. He fucked and was fucked by men. Nothing and no one seemed to ease his cravings, and at least once each day he got off by thinking about the man and his offer. Looking down at the semen splattered pages, he flipped to the last page, flicking his eyes down to the last line.

_If you agree to submit to me and accept me as your Keeper, call this number for further instructions._

The number differed from the one on the calling card the sheriff had given him the first time. Shaking his head, he folded the pages and tucked his cock back into his boxers before getting up to splash some water on his face. Looking at himself in the mirror for a long while, he wondered why the sheriff kept calling him pretty boy. _I’m just an average looking dude, aren’t I?_

Shrugging, he pulled off his boots and jeans and slipped under the covers, deciding to get some shuteye.

***

The next morning found Dean devouring a pancake special and some coffee at a local diner. The highway he was on forked a few miles up ahead. Depending on which fork he took, one would bring him closer to the man who could be his Keeper.

_Fuck, I can’t believe I’m seriously considering this._

Back on the road, he only had a short time to decide which fork he was going to take. Yet, in the back of his mind, he already knew. Dean wasn’t getting any younger, or prettier. It was a generous offer to share his home and food with a drifter like him. There was no denying the sheriff was a looker himself, with those dazzling blue eyes, but what kept drawing Dean back was that fucking magical cock. It had him bewitched; Dean couldn’t deny that.

As Dean approached the fork, he didn’t even hesitate as he changed lanes and headed back toward Sheriff Castiel Novak. When he was about an hour outside of town, Dean pulled over at a rest stop and fished out the pages and dialed the number. Somehow, it didn’t surprise him that there was a pre-recorded message on the other end.

_Hello, Dean. I knew you couldn’t resist calling. How many times did you read those rules, rights, and expectations before you got the nerve to call this number, I wonder? Never mind, if you have read them and agree, press one. If you read them, and want nothing more to do with me, press two. If you press two, just make sure I never see that pretty ass of yours near my town again, or I’ll make sure you regret it._

Hearing that sexy, gravelly voice went straight to Dean’s dick. Rolling his eyes at the threat, Dean smirked. He was tempted to be cheeky and press two, and still show up at the sheriff’s office, just to find out what would happen, but he decided against it. Pressing one, he held the phone back up to his ear to see what was next.

_You actually pressed one? I’ll admit that surprises me. There might be hope for you after all. I will be notified the moment this call ends. Come to the following address within twenty-four hours. I’ll be waiting._

Dean fished in his glove compartment for a pen and paper and scribbled down the address. As he was writing, he wondered if this was the sheriff’s home or the address of the local jail. _I guess I’ll find out when I get there._

Going into the rest stop bathroom, Dean freshened up and took the time to lube and plug his way too eager ass before heading back on the road, heading toward whatever fate that awaited him.

***

Pulling up to the house that his phone GPS had directed him toward, Dean took a deep breath to calm his nerves. It was a small, unassuming craftsman style house that sat at the edge of the small town. It was situated on a few acres of wooded land. That gave the sheriff a lot of privacy from neighbors. Slowly, Dean stepped out of his car and took in his surroundings as he retrieved his pack of belongings from the backseat. Seeing the woodshed next to the house made Dean’s heart skip a beat, as he imagined being led there for punishments. _Fuck_.

Swallowing thickly, he took in another deep lungful of air before making his way toward the front door. He knew the sheriff was inside, waiting for him. The parked patrol car outside of the house had confirmed as much when he was pulling up. His heart hammered in his chest as Dean made his way up the steps and across the porch toward the door.

Staring at the doorbell for a beat longer than he should have, finally Dean mustered the courage to press it before holding his breath. A moment later he heard footsteps approach and the lock on the door snick before it was pulled open before him. There stood Castiel, dressed casually in a pair of jeans and a soft grey cardigan, with the lapels of a white polo peaking over the collar.

“Hello, Dean,” Castiel greeted him. “Please, come in.”

Stepping inside, Dean looked around while Castiel closed and locked the door behind him. The entryway opened into a cozy living room with a couple of comfortable, overstuffed couches and a fireplace. Not sure what to do next, Dean just stood there as Castiel walked around him and turned, staring at him expectantly.

“Um, hi?” Dean said, not sure what he expected of him.

Crossing his arms, Castiel quirked an eyebrow at him. “Rule number 2, Dean.”

Dean closed his eyes, recalling the list of rules. _Oh!_

“Right here?” Dean asked, unsure.

“Yes, right here,” Castiel said, pointing at a small basket on the floor. “I expect swifter compliance of the rules in the future.”

Setting his bag down, Dean bent over to remove his boots, Dean nodded. “Yes… sir?”

“Good boy,” Castiel praised. “Yes, you may call me sir.”

Letting out his breath that he hadn’t realized he was still holding, Dean proceeded to remove his clothes, carefully placing them into the basket provided, while Castiel retrieved a pillow from the couch and set it on the floor in front of him. A flush of heat flared over his face when Dean slowly lowered his boxer briefs, revealing his rock-hard erection to Castiel. After Dean placed his underwear in the basket, Castiel merely nodded toward the pillow. “Kneel.”

Reaching out, Castiel ran his fingers through Dean’s hair gently for a moment before grasping firmly and tilting Dean’s face up. “I am pleased you decided to agree to my offer,” Castiel said, keeping his grip firm while fishing something out of his pocket. It was a leather collar, with a ring for a leash. Holding it up for him to see, he read the tag that dangled from it. _Dean._

“Do you agree to let me keep you, Dean?” Castiel asked.

 _Wow, I guess this is really happening_ , Dean thought. Flicking his eyes from the collar to Castiel’s face, he looked into the man’s lust blown eyes. His heart still hammered in his chest, and his mouth felt dry, but he knew this is what he wanted. “Yes, sir. I agree to let you be my Keeper.”

“Good boy,” Castiel praised, easing his hold on Dean’s hair as he fastened the collar around Dean’s neck. The distinctive scent of leather hit Dean’s nose as he buckled it into place, followed by the unmistakable snick of a small lock.

Castiel held up a tiny key. “I will keep this key with me always,” he said. “If there ever comes a day you wish to be released from our agreement, let me know, and I’ll unlock the collar.” Nodding in understanding, Dean reached up to feel the collar. Castiel allowed it as he carefully placed the key on a chain around his neck.

“Place your hands behind your back, pretty boy,” Castiel directed as he began to open his belt and unzip his jeans. “Now I promised to keep you well-fed. I’m going to give you a little appetizer to tide you over until dinner. Open that pretty mouth.”

Opening his mouth, the smell of Castiel’s arousal was heady as the man slowly slid his cock between Dean’s lips and over his tongue. When Castiel took his mouth last time, they had been outdoors, and Dean hadn’t noticed the man’s scent of arousal as much as he did now. There was something about it that was arousing and made his own dick twitch with anticipation.

Grabbing his head firmly in both hands, Castiel continued to slide his cock into Dean’s mouth and down his throat. Not for the first time, Dean was glad to not have a sensitive gag reflex, as he swallowed around the intrusion. “That’s it, good boy. I’ve been so hard ever since I was notified that you’d chosen to accept my offer. I won’t last long. If you swallow every drop, then I’ll give your ass a nice long fuck later.”

As Castiel pulled back, Dean took a breath through his nose, just before the man’s cock thrust back in, cutting off his airway. With his hands behind his back and his own cock ignored, Dean did his best to focus on breathing every time Castiel pulled back. Castiel set up a fast, hard rhythm that had his balls slapping Dean in the chin on every inward thrust.

Getting lost in the rhythm and focused on his breathing, Dean began to lose track of time. Dean’s eyes slid closed as he let this man, he barely knew, just use him for his own pleasure. He was pulled back down to earth when Castiel gripped his hair tightly and pushed his cock as deep as he could. “Swallow, pretty boy, uhn. Fuck! Take it. Swallow it all.”

Doing his best, Dean swallowed around Castiel’s cock as it pumped a load of semen down his throat. Castiel’s cock was shoved so deep, Dean never tasted it. Once Castiel had been milked dry, he withdrew his cock until just the head rested on Dean’s tongue. Lightheaded, it took Dean a moment to realize what Castiel wanted. Wrapping his lips around the softening cock, Dean licked and sucked it clean.

Giving a contented sigh, Castiel released Dean’s head and patted the top of it fondly. “That was perfect,” he praised. “I’ll be making use of that pretty mouth of yours more often from now on. Now up. Put the pillow back on the couch, pick up your things, and follow me.”

Still lightheaded, Dean wobbled to his feet and did his best to comply. Soon he was following as Castiel led him up a flight of stairs to the upper floor of the house. There was a hallway with four doors, and Castiel led him to the one at the end of the hall. “This is the master bedroom. When you’re good, you’ll sleep in bed with me. If you’re naughty, you’ll sleep in that cage in the corner. There’s also a cage in the basement for more severe behavior, but we’ll talk about that later.”

Looking around, the room was a decent size, with a large, cozy king-sized bed, a couple of dressers, and a large dog cage set up in one corner. There were two additional doors in the room. Castiel showed him the one on the right first, which turned out to be a large walk-in closet. It was only half-filled with clothing. “Set your bag on the shelf and you can unpack later. There’s plenty of room for your things, and since you’ll spend most of your time nude, you shouldn’t need much.”

Leading him to the other door, there was a well-appointed master bath with a tub and shower, two sinks, and a toilet. “You’re welcome to use this shower to freshen up after I show you the rest of the house.”

Behind the two of the other doors in the upstairs were bedrooms Castiel had converted into a home gym and office. The gym came complete with a treadmill and weight machine, with a TV hanging on the wall. The office had a large desk, one wall lined with books, and a cozy armchair in the corner. “I often spend my evenings in here reading,” Castiel explained. “I may have you warm my cock when I’m in here reading.”

The last door in the hallway led to a small bathroom.

Back downstairs, Castiel led Dean through the living room and adjoining dining room to a small but well-appointed kitchen that opened out to the dining room with a small island. “This used to be a small galley-style kitchen,” Castiel explained. “I knocked out part of the wall to open it up into the rest of the living space.”

Off the kitchen was a door that led to the back of the house. There was a small patio with a firepit and grill. Next to that door was a laundry room and a door leading down into the basement. The wooden stairs creaked as Dean made his way down behind Castiel to the musty smelling basement. It was unfinished, with shelves of boxes lining the walls. When Castiel led Dean around one set of shelves, Dean’s eyes went wide.

“We’ll discuss the use of this space in more detail later,” Castiel said as he stood to one side. “However, I suggest you behave yourself if you want to avoid finding yourself down here too often.”

Lining one wall hung a variety of painful looking straps, paddles, and whips. Hanging from the ceiling were a pair of wrist cuffs attached to a set of chains. Below them on the floor were steel ankle cuffs bolted to the floor, along with a drain. In one corner was another large cage.

“Yes, sir,” Dean agreed, trying to ignore the obvious twitch his dick just made.

“I should warn you, no matter how well-behaved you are,” Castiel said with a wicked smirk. “I guarantee, you will still spend some time down here.”

There went his dick, twitching eagerly again. This time Castiel saw it, based on the smug smile that crossed his lips. “Good to see at least part of you is on board with that idea. Now, go shower and then come help me with dinner.”

“Alright,” Dean said, turning to make his way back upstairs.

“Ah, ah,” Castiel scolded, giving Dean a pointed look.

“Oh, uh… yes, sir,” Dean corrected himself.

“That’s better,” Castiel said. “I’ll let that one slide, but don’t let it happen again.”

“Yes, sir.”

***

Sitting down with Castiel for dinner, Dean was still trying to process everything. Besides the blow job and having to be nude, everything felt so _normal_. He wasn’t sure what he was expecting, but he’d imagined that he’d be fucked senseless at least once by now.

Dean tried not to gripe at the dinner they prepared, which consisted of chicken breasts with a side of whole grain rice and some broccoli. Apparently, Dean’s new Keeper was a health nut. _What the heck have I gotten myself into?_ Dean asked himself as he stared forlornly at the bit of broccoli he’d picked up with his fork.

Chuckling, Castiel smirked as he happily ate his dinner. “I gather you’re not used to eating healthy. Don’t worry, if you’re good, I’ll allow you to eat some of your favorite foods on occasion. However, as your Keeper, part of my job is to keep you well-fed, and that does not mean stuffing you with junk food.”

“Yes, sir,” Dean replied as he began to eat his own dinner. It wasn’t completely terrible, but he was craving a burger and fries. _I should have treated myself at least once before coming here_ , Dean thought sadly.

“Do you have any questions regarding the list of rules I gave you?” Castiel asked.

Thinking about it for a moment, Dean slowly nodded. “Yeah, actually. Could you explain the difference between discipline and punishment, and what the heck is that bit about stress relief?”

“I was hoping you would ask about that,” Castiel said. “You will be disciplined regularly to remind you of your place. We’ll start off with once every day and based on your behavior, I may increase or decrease it. It will never be less than once every week.”

“How will you discipline me, sir?” Dean asked after he finished chewing on a dry piece of chicken.

“You’ll be given maintenance spankings. Typically, I’ll take you over my knee or bend you over a surface and warm that pretty ass of yours,” Castiel explained. “I will use an implement, anything from a hairbrush to my belt.”

“So, you won’t be using that room in the basement for this?” Dean asked, before taking a sip of water.

“No, the basement is meant for other purposes,” Castiel said wickedly.

“Like punishments?” Dean asked, remembering the woodshed he’d seen.

“Sometimes,” Castiel replied. “There will be a variety of punishments, and not always in the form of physical pain. For example, if you have an orgasm or masturbate without permission, your punishment would be to have your cock caged for a week. If you fail to complete your chores around the house, you will lose the privilege of watching TV. That sort of thing.”

“Wow, okay,” Dean said, sitting back and looking at Castiel. “I’ll admit, I wasn’t expecting that. I thought this would be all whips, chains, and sex.”

Laughing, Castiel wiped his mouth and shook his head. “No, pretty boy. As much as I would love to redden your backside and ravish you twenty-four-seven, that wouldn’t be realistic. I am still the sheriff of this town, and I can hardly leave you chained up in a cage all day while I’m at work. At least, I can’t do that to you all the time. However, that may happen occasionally, if your behavior warrants it.”

“Oh, okay,” Dean said before finishing the rest of his meal. Once he’d cleaned his plate, he looked back up at Castiel and asked. “What about the stress relief?”

“Oh yes,” Castiel said. “I included that because there are times when I come home from work and really need to blow off steam. That could just mean I need to have some fast, rough sex, but sometimes I might need to ask you to endure some pain for me.”

“How much pain?” Dean asked, recalling the implements he saw in the basement.

“That all depends,” Castiel replied. “I will promise one thing, I will never injure you. No broken bones, and I’ll try my damnedest to never break skin either. Taking pain for me is the ultimate sacrifice I’m asking from you. If that’s too much to ask, tell me now.”

Dean had taken his share of beatings over the years, so he was no stranger to pain. “I think I can take it, but what about safewords? What if I need you to stop?”

Castiel was silent for a long moment, before nodding. “Okay, fair enough. If it isn’t for punishment, and I’m asking you to take pain through no fault of your own, then you may use a safeword to get me to stop. We can figure that out over the next couple of days. I’ve taken some time off work so I can help you settle in.”

Fiddling with his water glass, Dean nodded. “Okay, that sounds fair. So, what kind of chores will I be doing while you’re at work?”

“I’ll expect you to help clean around the house and with maintaining the property,” Castiel explained. “I’ll ease you into everything tomorrow. You will not leave the property without my permission. In fact, I’d like for you to hand over the keys to your car. Driving into town will be a special privilege you can earn for being my good boy.”

Dean hesitated. That car was his one and only prized possession. “You aren’t going to take my car away from me, are you? It’s kind of special to me.”

“Of course not. It’s your car and will remain your property,” Castiel clarified, holding out his hand. “I am merely restricting your use of it. If we ever come to a point where this arrangement needs to end, I will permanently relinquish the keys to you.”

“Alright,” Dean agreed, as he stood up and made his way upstairs to retrieve the keys from the pocket of his jeans. Once upstairs, he went into the closet and reached into his jeans that were still in the basket he’d put them in earlier. Pulling out the keys, Dean stared at them for a long moment. The first wave of doubt hit him. _He’s a sheriff. He could impound Baby and take her away permanently if he decided to, couldn’t he?_

Shaking his head to clear it, he slowly walked down the hallway and down the stairs, until he stood before Castiel. “I… I’ve never let anyone else have the keys before, sir,” Dean admitted as he clutched them close to his chest. “Promise me you won’t impound her or auction her? She also needs a lot of TLC so can you include car maintenance as part of my chores, please?”

“Just let me know when you need to work on her, and I’ll make sure it’s included in your schedule,” Castiel readily agreed. “As I said, she’s your property. I won’t take her from you. You let me know when you need something for her maintenance, and I’ll supply it. Okay?”

Feeling the tension in his shoulders ease, Dean nodded and placed Baby’s keys into Castiel’s outstretched hand. “Okay. Thank you, sir.”

“Go back up to the bedroom and kneel by the foot of the bed for me,” Castiel instructed as he slid the keys into his pocket and began to clear the dishes. “I’ll clean the kitchen and join you shortly.”

Nodding, Dean padded his naked behind back up to Castiel’s bedroom. Not sure which way he should face, he opted for kneeling sideways next to the foot of the bed. He was grateful that the man had plush and well-padded carpeting as he sank to his knees. His hands traveled up to his throat to fiddle and adjust the collar. It was a well-made collar and not just some cheap pet store kind.

 _I wonder how long he’d been planning all this?_ Dean wondered as he fingered the tag with his name on it. _How’d he know I’d come back and agree to his wacky proposition?_

Dean had to wonder if there had been other _pretty boys_ before him. If there had been, did they choose to leave or did Castiel grow bored and send them packing? The man didn’t seem like he’d treat anyone cruelly, but maybe that came later. With all the sadistic equipment in the basement, it was certainly possible.

Before Dean’s mind could swirl completely out of control, Castiel arrived, closing the bedroom door behind him. Walking over, he ran his hand through Dean’s hair before giving it a little tug. “Hmm, I think we’ll let this grow out. I like to be able to get a good grip when I’m fucking.”

A whimper escaped Dean’s throat at that image, as his eyes adjusted their focus onto the sizable bulge inside Castiel’s jeans. “Be a good boy and fetch me the hairbrush from the bathroom counter.”

Stumbling to his feet, Dean went to fetch the hairbrush. The earlier conversation flashed through his mind and he realized exactly what the hairbrush was going to be used for. It was a solid wooden brush with black bristles, with a few strands of Castiel’s hair entwined. He took note of the heft of the brush as he carried it over to where Castiel sat on the edge of the bed.

“Thank you,” Castiel said, with a wicked twinkle in his eye. “Now bend yourself over my knees. It’s time for your first discipline session. I’m going to warm up that pretty ass of yours.”

Swallowing thickly, Dean handed over the brush. As he bent over Castiel’s knees, Dean felt all the blood rushing south as his dick decided it was very much on board with the proceedings. Dean didn’t know he had a masochistic kink before the sheriff had whipped his ass the last time he’d come through this town.

Castiel helped get Dean settled over one knee, while his other leg pinned Dean’s legs down. With the way he was positioned, Dean’s cock rubbed against Castiel’s leg and his ass was well presented for the spanking it was about to receive. With one arm wrapped around Dean’s waist to keep him still, Castiel wasted no time. The hairbrush cracked against his ass, making Dean yelp at the sharp sting.

Not pausing to let Dean appreciate the tingling warmth of the initial sting, Castiel laid into his ass with a rapid-fire succession of smacks, peppering Dean’s ass and thighs. There was no rhyme or reason as to where the blows landed, only the rhythmic staccato of smacks as each hit with a smarting sting.

A blistering heat began to form as smacks overlaid smacks until Dean’s entire world was narrowed down to the focus of the searing intensity of the spanking. His hips began to buck, trying to escape the unending rain of smacks, causing his cock to drag across Castiel’s leg, sending sparks of pleasure mixed in with the pain. With every smack, Dean’s ass tightened around the plug he still wore, stimulating him even further, and Dean’s brain short circuited as pain and pleasure mixed.

“That’s it, pretty boy,” Castiel said. “Hump my leg like a dog, while I make sure your ass knows who owns it now.”

Dean’s face flushed hot, embarrassed to have been found out, yet unable to stop himself from dragging his cock against Castiel’s still-clothed leg. The mix of pain and pleasure melted together into a transcended experience, and Dean hadn’t even been fucked by that glorious dick yet.

Losing himself in the moment, Dean didn’t even notice when the spanking ended until he felt something cold drizzle over his abused ass. Castiel massaged whatever it was gently into his ass, as the heat from the spanking rose sharply.

“You took that very well, pretty boy,” Castiel praised, releasing him from his grip. “Are you going to be good and take your fucking like a good boy?”

Standing unsteadily on his feet and unable to form words, Dean nodded. Castiel rose and put away the hairbrush, coming back with a towel that he spread onto the bed. “You’re not allowed to come without permission. I’m going to test your self-control tonight. You do not have permission to come while I’m fucking you. If you succeed, I’ll give you the best damned blowjob you’ve ever had. If you fail, I’ll milk you and lock your cock in a cage for a week. Understood?”

A shudder ran through Dean as his mind processed that mental image. “Y… yes, sir.”

“Good boy. Now, up on the bed, on your hands and knees.”

Crawling onto the bed and centering himself on the towel, he presented his hot, throbbing ass to Castiel. “Fuck, your pretty ass looks so good like that,” Castiel said with admiration. “Scoot back, I want to be standing when I take you.”

Dean obeyed, until Castiel’s hands halted him, grasping his hips, and running his hands over his hot flesh. “Fuck, you have the perfect ass,” Castiel praised, giving Dean a few playful smacks to his already smarting backside. Then Dean felt his plug being removed and set on the towel next to him.

“I have a plug that can be locked inside you,” Castiel stated conversationally, even as he plunged two fingers into Dean’s ass. “That’s another possible punishment, to make you ask permission to do something as simple as take a shit.”

Dean whined as Castiel’s fingers found his prostate and massaged it vigorously. “So, you better be a good boy for me and don’t come.”

The fingers withdrew and Dean heard the distinct jangle of a belt being undone, followed by the lowering of a zipper. Looking behind him, he stared as Castiel pulled his rock-hard cock out of his jeans and began slicking it up with a bottle of lube he held in his other hand.

“Eyes front,” Castiel commanded as he approached Dean and grasped one hip firmly. “Focus on your Keeper’s pleasure, not your own, and you will be rewarded.”

Nodding, Dean gripped the towel he knelt on tightly while his ass was filled with that glorious dick. Once fully sheathed, Castiel held himself flush against Dean’s reddened ass. “I want you to focus and squeeze me.”

Concentrating on the massive intrusion in his ass, Dean did his best to tighten his muscles around it. He felt a surge of satisfaction when he heard Castiel groan with pleasure. “Yeah, that’s it. Keep doing that, every time I bottom out, squeeze me like that.”

Grateful for the distraction, Dean did his best to comply. Castiel slid out and back in slowly, and Dean focused on squeezing his muscles when he felt Castiel’s balls against his perineum. Castiel began to thrust into Dean again and again, speeding up only slightly. He let out a filthy groan every time Dean squeezed around him.

Trying his best to time his squeezes on every inward thrust, Dean was doing his best to ignore the growing coil of pleasure building in his own body. His cock was painfully hard, and he desperately needed release. Castiel didn’t seem to be in a hurry to reach his own end, and since he’d come down Dean’s throat not that long ago, Dean had a feeling the man was going to take his time. _Fuck._

“Please, sir… _please_ ,” Dean cried out.

Castiel grabbed him by his hair, gently pulling his head back. “Please what, pretty boy?”

Hedging his bets, he opted to beg for his Keeper’s pleasure over his own. “Please… come, sir,” Dean begged. “ _Please_.”

Castiel shoved into him deep and hard, gripping his hair tightly for a moment. “I intend to enjoy your ass for as long as possible,” he growled before the hand in his hair softened its grip. “But you have been doing your best to be good. This is your first night as my kept boy, so I’ll be lenient. You may come, but you cannot whine about being oversensitive when I keep fucking you afterward. Deal?”

Relief flooded through Dean as he slumped down to his shoulders on the bed. “Yes, sir. I won’t complain. Thank you.”

“I wouldn’t be thanking me just yet,” Castiel said wickedly, as he resumed fucking Dean. The angle of the thrusts changed as Castiel seemed eager to bring Dean to his orgasm, the man’s hipbones crashing painfully into Dean’s tender ass. No longer afraid of disobeying his Keeper, Dean let the pleasure build to a crescendo as that glorious dick kept pounding into him.

Dean screamed in ecstasy when his orgasm slammed into him. His cock spurt untouched, rope after rope spilling onto the towel beneath him. His hands clenched, his toes curled, and his entire body shuddered as his orgasm was prolonged by the cock still fervently fucking him.

A few more thrusts later, and Dean understood why Castiel had agreed to let him come. The man continued to pound into his prostate, which was now bordering on hypersensitive. Letting out a whimper, Dean reminded himself not to complain.

With a wicked chuckle, Castiel gave Dean’s ass a hard slap while thrusting in even harder. “Wishing you had waited to come, aren’t you pretty boy?”

Unable to keep his knees under him, Dean collapsed, barely nodding in response to the question. He keened while Castiel began to fuck him roughly. It was all too much, and he couldn’t help the sounds he made as his ass was pounded into the mattress, his oversensitive cock being rubbed against the wet, sticky towel beneath him.

Thankfully, the hypersensitivity slowly eased and being fucked began to feel good again. Valiantly Dean’s cock tried to rise to the occasion as it kept being rubbed between the towel and Dean’s sticky abdomen. Castiel slowed his thrusts and let out a filthy groan, making Dean think he might have come. Instead, Castiel slid his still hard dick out of Dean’s ass and flipped him over onto his back, grabbing him by the thighs and folding Dean in half before slamming back into him.

“I’m getting close and I want you to see my face when I fill that pretty little hole of yours,” Castiel said with a growl. “Keep your eyes on me, pretty boy.”

Flicking his eyes up at Castiel as he began to fuck into him again took Dean’s breath away. The look of sheer ecstasy on the man’s face made Castiel look beatific. After always being taken from behind, Dean didn’t expect to get lost in those lust-blown, sapphire blue eyes as Castiel continued to take his pleasure.

When their eyes met, Castiel’s hips stuttered to a stop. He leaned forward, grabbing Dean’s hands, and pinning them over his head. Grinding his cock inside of him, Castiel’s breath came in ragged gasps that Dean could feel puff against his face. Castiel’s eyes flicked between Dean’s eyes and lips, while grinding even deeper. Dean let out a needy whine and Castiel leaned all the way forward and captured his mouth.

This was new. Somehow, he’d never imagined that they’d kiss. This was all some sadistic sex game, right? Kissing was more intimate. Yet, Dean soon lost himself in the moment as Castiel’s lips pressed against his, while his tongue plundered his mouth. The added level of intimacy stirred something deep inside of him he struggled to comprehend. All Dean knew was that suddenly his arms ached to wrap around Castiel and pull him closer, making him struggle against the grip the man had on his wrists.

Not understanding the source of Dean’s struggle, Castiel broke the kiss and gave him another wicked smile. “Remember, focus on your Keeper’s pleasure,” Castiel reminded him. “Just take your fucking like a good boy.”

Castiel released Dean’s wrists and wrapped his arms around Dean’s thighs, pulling him closer before fucking into Dean hard. He set a brutal pace, slamming his hips into Dean hard and fast. Dean whimpered at the renewed fervor of their coupling, his cock stirring fully back to life as his prostate was again being targeted. He couldn’t remember the last time he’d gotten hard twice in a row this quickly.

“Look at me, pretty boy,” Castiel demanded as his fucking became frantic.

Dean’s eyes found Castiel’s again, at the same moment that Castiel fully sheathed himself and shouted his release. Dean felt the man’s cock pulse deep inside of him. To see the moment of pure ecstasy on his Keeper’s face was breathtaking. Dean had never seen a man look more beautiful.

Coming down from his orgasmic high, Castiel smiled brightly at him. “You take my cock so well. I swear I’ve never had orgasms this good before your pretty ass came into my life.”

Dean tried hard not to roll his eyes at Castiel’s declaration. Instead, he merely gave a tired smile. Dean was both wrung out and still horny. He now lamented the fact he would likely not be allowed to come again when Castiel surprised him. Letting his softening cock slide out of Dean’s hole, Castiel slid to his knees, pulling Dean even closer to the edge of the bed. Without a word, Castiel wrapped his lips around Dean’s cock and began to suck. Using one hand to jerk his shaft, Castiel expertly licked and sucked at the head. Dean threw his head back, not understanding why Castiel was doing this, but definitely not complaining.

His hips twitched while Castiel kept sucking him. Dean was close, but not close enough. Letting out a whine of desperation, Castiel slid two fingers into Dean’s well-used hole, rubbing his prostate again. That did it. Dean saw stars as his dick pulsed a load of seed into Castiel’s mouth, the man swallowing every drop.

Letting Dean’s cock slide out of his mouth, Castiel grinned at him like the Cheshire Cat, while giving Dean a moment to catch his breath. Castiel eventually stood and pulled Dean to his feet as well. “Let’s take a shower. We can’t go to bed all sticky.”

“Yeah,” Dean agreed, following Castiel.

Once in the shower, Dean slumped against the tile while Castiel stood under the hot spray of water. “Man, you’ve got some stamina.”

“That’s why I had you suck me off earlier,” Castiel said with a smirk. “I also took something to help.”

Dean’s eyes widened at that revelation. “You popped a little blue pill just so you could fuck me into next week?” Dean asked with a laugh.

“I wanted your first time as my kept boy to be memorable.”

“Wow, was it ever,” Dean admitted, straightening up. “Uh… permission to give you a hug, sir?”

Cocking his head, Castiel regarded him for a moment. “Why?”

“I just kind of want to?” Dean said sheepishly. “Also, back when you were kissing me, I just really wanted to wrap my arms around you. I kinda still do.”

“I had no idea you were so sentimental,” Castiel said as he turned. “Alright, you may hug me, but then you’re washing my back.”

Smiling to himself, Dean wrapped his arms around Castiel and laid a quick kiss on the man’s shoulder. “Yes, sir.”

***

**Epilogue: Thirty years later**

Dean grabbed the mugs of coffee he’d just poured and walked out to the front porch, handing one mug to Castiel. “Here you go, sir.”

“Thank you, my pretty boy.”

Running his hand through his shoulder length salt-and-pepper hair, Dean laughed. “I’m not that pretty anymore, sir.”

Turning to face Dean, Castiel reached out to stroke his now age-worn face. “You’ll always be my pretty boy, Dean.”

Leaning his forehead against Castiel’s, while Castiel ran his fingers over the collar Dean still wore, Dean smiled. “Thank you, sir.”

Castiel pulled Dean in for a slow, deep kiss, finishing with an affectionate peck on his nose, making Dean’s face flush with affection.

“Now, finish your coffee,” Castiel commanded, giving him a wicked smirk. “This cock won’t suck itself.”

Laughing and shaking his head, Dean gulped down his coffee. “No, sir, I don’t suppose it will.”

**Author's Note:**

> Thank you for reading, and I hope you enjoyed this lovely smutfest. This concludes this series. Before anyone asks, if I feel inspired, I may add some timestamps, but I cannot promise anything.
> 
> In the meantime, I have some novels to get back to writing.


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